The Only 2 Questions To Ask If You're Thinking Of Leaving Your Job

Hey everyone,

Oh, that grass, it’s always greener, isn’t it?

Whether they admit it or not I’m going to guess everyone thinks about changing careers. Eyeballing job postings, dreaming of working abroad from some South American hostel, wondering if it’s time to ask the big boss for a promotion into the open role sitting right above you.

I spent 10 years working at Walmart and over the course of those years I thought many times: “Should I do this, should I do that, should I apply for a role inside, should I apply for a role outside?”

When I left Walmart so I could focus on writing I called up my old boss ​Dave Cheesewright​ who gave me two helpful tests to make the decision.

Now, before I share the tests, I don’t want you to get me wrong. Sleepless nights, mental flip-flopping, moments of anxiety, that’s all part of it too. The goal is not to eliminate that vast array of emotions you’ll feel as you go through a career change. It’s a big decision! And it has huge consequences. Those emotions provide red, yellow and green lights along the path.

But the goal of these two tests is to eliminate any endless contemplation, to help rudder yourself, and just make sure you’re steering your life the right way.

So what are the two tests?

1. The Deathbed Test. You need to ask yourself: “When I’m looking back on my life, from my deathbed, which one of these options will I regret not doing the most?” Use that answer to helpfully guide you. In her book ‘The Top Five Regrets of the Dying,’ palliative care nurse Bronnie Ware shares that the No. 1 regret in life is “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

2. The Plan B Test. This is a simple question: “What is my Plan B?” This is the what if it fails test. You have to fully contemplate that failure. Plan for it, envision it, live through it. Could you go back to your former job or former company? Would you go get that degree you always wanted or move to Spain and take that painting class? Or would the bottom fall out of your finances completely? Your Plan B must be comfortable enough to prevent you from freezing you into risk-averse behavior after you make your move. Because if you’re picturing an empty bank account, you won’t take the chances you need to take to be successful in your next act.

For me I was thinking about whether I wanted to leave a big company to work as an author. My Deathbed Test told me “You better do this! You’ll regret it if you don’t!” and My Plan B Test told me “Well, it won’t be pretty, but if this whole thing falls to ruins, I guess I’ll polish the resume, knock on doors, and try and find another job.”

It didn’t sound so bad when I put it that way.

I hope these two tests help you along your path.

Good luck,

Neil


There's one more principle I like to apply in these situations...the "​HELL YES!​"

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